


Close Your Eyes

by Jetsetlife138



Category: IT (Movies - Muschietti), IT - Stephen King
Genre: Alcohol Abuse/Alcoholism, Anal Fingering, Anal Sex, Angst and Hurt/Comfort, Arachnophobia, Barebacking, Blow Jobs, Brutality, Childhood Trauma, Come Swallowing, Daddy Issues, Daddy Kink, Dark Character, Dead Dove: Do Not Eat, Emotional Hurt/Comfort, Emotional Manipulation, Explicit Language, Explicit Sexual Content, First Time Blow Jobs, First Time Topping, Fluff and Angst, Hair-pulling, Hallucinations, Hand Jobs, Hiding Trauma With Humor, Human/Monster Romance, Implied/Referenced Child Abuse, Implied/Referenced Drug Use, Lemon, M/M, Multiple Orgasms, Nipple Licking, Past Abuse, Recreational Drug Use, Rimming, Rough Oral Sex, Scary Clowns, Seduction, Suicidal Thoughts, Tentacle Sex, Tentacles, Violent Sex, Violent Thoughts
Language: English
Status: Completed
Published: 2020-07-30
Updated: 2020-07-30
Packaged: 2021-03-06 05:47:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 12,581
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25618333
Author URL: https://archiveofourown.org/users/Jetsetlife138/pseuds/Jetsetlife138
Summary: Desensitized due to years of abuse and neglect from his father, Tyler is in search of something to make him feel alive. Derry’s very own sewer-clown targets him as easy prey. However, much to his vexation, he is unable to elicit fear from the dejected man. Subsequently, Tyler is captured by Pennywise, which results in an unintentional bond.
Relationships: Pennywise (IT)/Original Character(s), Pennywise (IT)/Original Male Character(s)
Comments: 1
Kudos: 61





	Close Your Eyes

**Author's Note:**

> Commission Request
> 
> Inspired by "Close Your Eyes" by Kim Petras

Rain fell from the dark, starless sky as he gazed out at the jagged city skyline. Hot tears blended with raindrops as they silently streamed down his face, fogging up his glasses from the heat of his skin against the chilled air. He made it a point to breathe through his nose to avoid sobbing as he leaned on the rail of the porch for support. He wasn’t even sure why he was crying in the first place. At some point, it all just became too much. The weight in his chest where his heart should have been was instead filled with a tarnished, shriveled up hunk of scrap, slowly descending deeper and tearing him apart from the inside. 

Sucking in a shaky breath, he released it slowly as he ran a hand through his wet, sandy blonde hair in an attempt to calm himself. The loud, muffled music thumping from the house was beckoning his return. He had a role to play. He couldn’t allow anyone to see him like this… but he needed a reprieve. Regardless of the fact that he was surrounded by people, sometimes the loneliness crept in and consumed him entirely. Rather than confide in anyone, he thought it best to step outside and collect himself away from anyone else. 

Swishing around what was left in his red solo cup, he tipped it back against his lips and guzzled the remains. He wiped his mouth with the back of his sleeve carelessly enough that he almost snagged the material on his lip ring. His mind was muddled from emotion, alcohol, and whatever other substances he had consumed that night. He could hardly even remember taking the pills someone had given him with promises of enlightenment after he consumed them. Maybe that’s what caused his unwelcome tears. It was worth the price, though. Anything to numb the pain, which seemed to have clawed its way back to the surface, regardless of his many attempts to suppress it. 

Tyler was thoughtful for a moment. Why was he even there? He didn’t want to be. He loathed the fact that the only reason he was invited to those sorts of things was because he was the ‘funny guy’ and was seen as a somewhat decent source of entertainment. Even so, parties were supposed to be fun, right? So, why wasn’t he enjoying himself?    
  
It was pointless. The search for purpose in his life was endless and disappointing; useless in every way. Tyler spent his days searching for anything to make him separate the pleasure from pain, rather than be consumed by the nothingness that plagued his body and mind.    
  
The thought that kept him awake most nights was the fact that no one ever wanted him. He wasn’t a priority in anyone’s life. He was just a stupid, broken boy who didn’t deserve happiness.    
  
Laughing softly to himself, he realized that his mood was shifting into something much lighter and significantly less morose. Finally, something he took must have been kicking in, creating a fabricated illusion of cheerfulness that he wanted to bask in. A clamor from inside the house was followed by roars of laughter, indicating something entertaining occurring. Probably a winning hand at strip poker or something stupid like that.    
  
Tossing his empty cup aside, he shook himself out to get his bearings. Tonight was going to be different. He wasn’t about to waste another minute being somewhere he didn’t want to be, especially when he was feeling so upbeat and free. 

His footsteps were heavy on the sidewalk as he walked through the dimly lit alley. The party had been up in the hills at the house of some guy he worked with, and he needed to make his way back to civilization where something better was waiting for him. Wondering where he could go, his first thought was just to go home and ride out the high on his own. No, wait. He couldn’t go home. Not the home he wanted. Home wasn’t his dingy apartment anymore. It was once again his childhood prison that had belonged to his father. Well, at least it did until he died two months ago from a heart attack. Served the bastard right.    
  
The residence was left to Tyler, and with it, the traumatizing memories of his youth. He didn’t want it, but it was better than a roach-infested, closet-sized apartment that he was paying out the ass for.    
  
His mom died when he was young and he couldn’t remember much of her. Tyler’s father took his grief out on his own child, finding any excuse he could to lay his hands on him in aggression. It left more of a mark than just a few cuts, bruises, and broken bones. It left a mark on his soul that would darken his life forever. 

Tyler moved out the first chance he could get. On his sixteenth birthday, he packed a bag and barely escaped with his life when his dad found out what he was up to. The intoxicating substances muffling his brain caused an inappropriate chuckle at the distressing memory.    
  
Marching forward, he slipped his freezing hands into the pockets of his hoodie, watching the raindrops dance on the asphalt before him. He barely registered the dampness of his clothes as he relished in his high. It was a seldom moment where everything made sense, and life was beautiful. It was almost better than dreaming. 

Glancing towards the sky, the rain came down like falling stars, flooding the Earth with life. Mother nature nurturing her young. The mother Tyler had always wanted, but never had. A deep, true love that ignited his soul and awakened his spirit, which had been broken time and time again, leaving nothing behind but a hollowed out shell of a man.    
  
Taking off his glasses to remove the droplets that impaired his vision, he peered over the horizon at the city below. The lights glimmered before him, similar to that of thousands of fireflies dancing in the distance. Between the gleaming lights were vacant streets, offering nothing but more loneliness. It was then that Tyler happened upon a bridge, made from wood and iron. Hard and cold. Just like him.    
  
Casually positioning himself against the railing, he looked down towards the sloshing waves, their motions beckoning enticingly. Before he could register his actions, he was positioned on top of the rail, his knees wobbling as he found his balance. His breath caught in his throat at the excitement of it all. There was no fear. Whatever happened, there would be no regrets. Only peace.    
  
Running his tongue along his lip, he tasted the rain. Earthy. Natural. Just as he was sure the waves beneath him would be. Tyler recalled a time as a child where he went swimming in a river that no one else dared venture into due to the freezing temperature of the water. He was unfazed as he dove in, allowing his body to acclimate to the icy current, which soon became warm and comforting around him. He wondered if that’s what would happen again as he met the waves below his feet. That was where he should be. But would it accept him? Or would the river reject him like the rest of the world had.    
  
Holding onto one of the posts beside him, he hurled himself around it, one of his feet leaving the rail and swinging him around. When he landed, his foot slid on the wet surface as it made contact with the rail once again, but he caught himself quickly, his body reacting in a way his mind couldn’t keep up with. His subconscious scolded him then. A warning. He was meant to fear death, not run towards it. But there was no fear anymore. There never would be again.    
  
Would death really be so bad? No one would care, right? Maybe. He was the funny guy, after all. He perfected the art of masking his trauma through humor. It was a natural gift, he supposed. Making people laugh gave him a purpose he otherwise didn’t feel that he had. Tempting gravity, he snuck closer to the edge. They would understand soon enough.    
  
Canting his head back, he noticed something out of the corner of his eye. A figure was approaching him, emerging seemingly out of nowhere. Tyler wondered if it was just another straggler from the party that he himself stumbled from, but he didn’t give it another thought. He wouldn’t allow the stranger to shatter the perfect moment he was having.    
  
Turning back around, he stretched a foot out flirtatiously over the waves that called to him still. He would wait for the man to pass, he decided. If he was out here alone, he must be trying to find his way, too. Just like Tyler. They were alike in that aspect. Kindred spirits, gravitating towards the alluring River of Souls. Maybe they were all spirits, floating around in limbo trying to find a purpose. Except Tyler found his, and he was about to dive head first into it.    
  
The man didn’t pass. Instead, he stopped, just a few feet away and watched with interest. Tyler could feel his eyes on him as he leaned out further, gauging the time it would take between his release of the bridge to the moment he would hit the water.    
  
The rain stilled then, as if the sky itself was holding its breath in anticipation for Tyler’s descent into oblivion. He was ready. This was it. It was time.    
  
“Such a waste,” the stranger chimed in a startling sing-song voice. “Waste of blood. Waste of flesh. Waste of fun.” His voice was clear and sharp. Tyler could easily detect every word - every syllable.    
  
Turning towards his audience, Tyler scowled at the man only to discover who-… or  _ what  _ he was.    
  
He was a clown. A menacing one at that with a dirty, tattered, and faded costume, complete with an elegant poofy collar. Tyler's gaze trailed up towards the clown’s pale face with red lines etched across his lips and eyes. The clown’s hair was a fiery auburn, shining bright even in the darkness. His eyes were vivid, golden and greedy, looming at Tyler like he was a meal.    
  
Of all the things he expected to see, that wasn’t it. He must really be fucked up to be seeing clowns in the middle of the night. Unless, the clown came to bid him adieu. That must have been it. His subconscious created the epitome of humor to mock him in his last moments, pushing him over the edge both literally and figuratively. He would comply.    
  
Just as Tyler was about to take the leap, he felt a tickle on his hand. Halting his movements, he peered down towards his hand, which had been the only part of himself holding him onto the rail. His breathing ceased and the blood drained from his face when he saw not one… but multiple spiders that were crawling from the post, onto his hand, and up his sleeve.    
  
Releasing a dramatic yelp, he impulsively released his grip on the bridge, tripping on his own feet and falling hard towards the water. Panic struck his every nerve as his scream caught in his throat. He closed his eyes, ready to accept his fate, when a harsh tug pulled him back.    
  
Before he could comprehend what happened, he was back on solid ground. Opening his eyes, he could see the bridge in the distance, yards away from where he was standing, which didn’t make any sense considering he had been falling from that very bridge not five seconds ago.    
  
A firm grip on his arm pulled his focus, causing him to peer into those golden eyes that seemed to glow in the darkness. “Hiya, Tyler!”    
  
Everything was fuzzy, but he could feel himself sobering a bit after that ordeal, and yet the clown was still there. He was losing time. Either that, or he really did fall, and this was his afterlife. Or, alternatively, none of it was real at all and he was still back at the party passed out and hallucinating. 

“This isn’t real enough for you, Tyler?” the clown mocked, as if reading his mind. His tone was sympathetic, but he had a wry grin on his face. “ _ I’m _ not real enough for you?”   
  
If this was a dream, there really was no reason to be afraid. Not that Tyler would be anyway. He’d lost all sense of fear long before that night. After what he had endured, there was no point in fearing anything, let alone a murderous-looking clown. 

Tyler turned towards the clown, who still hadn’t relented his grip on his arm. Sniffling due to the chilled air, he took a moment to look him up and down, pushing his glasses up the bridge of his nose to focus more. When he met the clown’s eyes once again, he couldn’t help his grin.    
  
Something about the way the clown was looking at him stirred something deep down inside of him. The clown made a motion to wave at him, but Tyler placed his hand in his, weaving his fingers in between the other man’s gloved ones. He noted that the clown’s hands were so much bigger than his own and they weren’t warm like he figured they would be.    
  
“What’s your name?” Tyler slurred.    
  
The clown sneered at the intoxicated man, a hint of amusement in his eyes as he allowed Tyler to touch him. “Why, I’m Pennywise, the dancing clown!”   
  
“Pennywise, huh? What happened, did you lose track of your circus?” 

The clown smirked back at him, leaning in to brush his face along the stubble of Tyler’s cheek as he whispered into his ear. “Play a game with me, would ya?”    
  
If Tyler had been sober, he would have been better at hiding the embarrassing groan that escaped his throat as he bit his lip. Something about the way Pennywise was pressed against him and huskily whispering enticing words into his ear made his knees weak. God, could he have been any more obvious?   
  
Tyler splayed his hand on Pennywise’s chest, running his fingers through the fluff of his red tufts before sliding his hand up. His act of intimacy was interrupted when he stumbled on his own feet and fell into the clown, grateful for Pennywise’s quick reflexes as he caught him with ease.    
  
“Come join the clown, Tyler,” the clown demanded in a low and dangerously alluring voice. Tyler couldn’t deny the fact that he was getting turned on. Despite the fact that this was a stranger in a creepy clown get-up, it seemed as though he wanted to take care of Tyler. As if all Tyler had to do was trust him and he would lead him to comfort. He would watch over him and protect him. Was that what having a real father felt like? Those comforting feelings were foreign to Tyler, but he was enjoying it. 

Tyler grinned at the clown’s offer. “Whatever you say, Daddy.” He had only meant to tease, but was shocked when the clown lifted him like a child, cradling him against his chest as if he weighed absolutely nothing. Tyler couldn’t recall the last time he had been held like that. Maybe not ever.    
  
Their eyes locked, the clown’s icy stare burning with intensity as Tyler trembled against him. He could have sworn that he heard the clown growl at him. Fuck, that was hot. He was so strong. He made Tyler feel precious and safe. Even as Pennywise walked, his eyes hardly left Tyler. He looked like he was ready to ravish him, which he wasn’t complaining about. At one point, Tyler thought he saw a droplet of drool spill over the clown’s full red lips with eager anticipation, which excited Tyler even more. 

No one had ever looked at him this way. No one had ever shown an obvious hunger for him, and he was eating it up like a man starved. Which, he was - starved for affection. Ready to willingly give himself over to this man who would clearly give him everything in return.    
  
“So soft and warm,” Pennywise cooed as he continued to carry Tyler. He wasn’t even paying attention to where the clown was going. Happy and compliant, he made no effort to look at his surroundings. “Perfection. Oh so tasty…”    
  
In no time at all, they were suddenly in front of Tyler’s front door to the home he despised. “How did you know where I lived?” he stammered, regaining clarity for a moment.    
  
Pennywise put him down, towering over him threateningly. Tyler wasn’t short by any means, so he figured that the clown must have been freakishly tall. “You’re not afraid.” It wasn’t a question. He was simply stating a fact.    
  
“Do I need to be?” Tyler countered, trying to balance himself as his vision spun with intoxication.    
  
“Not yet,” Pennywise grinned so widely that it shouldn’t have been possible. In fact, it looked horrifically unnatural. “But you will be.”    
  
The blood drained from Tyler’s face as Pennywise’s body began to contort, the snaps and crunches of his bones loud and prominent in the quiet night air. His pale skin began to darken while he started to sprout additional limbs, slimming in size and elongating to support his growing body. His two eyes broke apart multiple times, resulting in several beady eyes glaring at Tyler with nefarious intent.    
  
Within another second, the clown was gone, and in his place stood a monstrous-sized spider, baring its fangs at Tyler as he pushed himself up against his front door, not even having the ability to scream out of shock.    
  
His hand fumbled with the front door knob as he thrashed his wrist around, knowing that he thankfully left it unlocked. Finally getting it right, the latch released and Tyler nearly fell through the door as it opened harshly against his weight.    
  
Without taking another look behind him, he stumbled through the front door, slamming it behind him and dashing towards the back where his bedroom was. He flung himself into his bed, tossing the covers over himself and sat in the fetal position, hyperventilating.    
  
It was a bad trip. That’s all it was. Though his high had begun so wonderfully light and comforting, it had flipped so quickly, betraying him into seeing his absolute worst fear. There was very little in this world that Tyler was genuinely frightened of. Spiders were one of them.    
  
“Tyler…,” an ominous, gurgling voice pierced through the tense air. Tyler dared to glance out from the covers, feeling like a terrified and helpless child. Looking up towards the door frame, his heart skipped a beat when the unmistakable figure of his deceased father was standing there, leering back at him.    
  
The young man shuddered, knowing that none of this was real and that it was just a hallucination. In addition to that, his father didn’t scare him anymore, so this was a less terrifying apparition than the spider had been.    
  
A low chuckle echoed from behind him and he found himself becoming more aware. He reached beneath his glasses so that he could rub his eyes with his fists in an attempt to clear his vision. It did no good. The walls around him started to blur and melt, revealing a dark and dank chamber where his bedroom used to be. It was clear now. He wasn’t at home. He was nowhere near it.    
  
An acrid stench assaulted his nostrils, causing him to cough at the potency of it. He tried to take a deep breath through his mouth, but somehow that made it worse. Another cackle rang out through the chamber, echoing hauntingly.    
  
Looking around, his eyes started to adjust to the darkness. The damp air was rancid and he could hear running water somewhere in the distance. The walls were dripping with what he had hoped was only water, leaving puddles on the floor.    
  
Tyler could feel himself sobering so… why was he still underground? Wasn’t it an illusion? There’s no way he could have just mindlessly wandered down there.

He jumped to his feet, his head still spinning, causing him to lose balance for a moment, but he quickly caught himself. He was able to get his bearings as he looked for an exit. Across the chamber was a large pipe, big enough to fit a person. That seemed to be the only way out.    
  
Propelling himself forward, a blur of motion in the corner of his eye distracted him. Before he could react, he collided with a firm wall of silk. Stumbling back, he realized that he had smacked right into Pennywise who was grinning maniacally at him.    
  
Tyler fought off the feeling of shock as he steadied himself. He was done with this bullshit.    
  
Before he could bitch out the clown, the creature’s hands wrapped around his neck, choking the life from him. “Close your eyes if you don’t believe, Tyler,” he snarled, maintaining his relentless grip on his throat. “Close them and see!” The clown’s eyes glowed with hunger and hostility as he unhinged his jaw, revealing a mouthful of fangs rather than the buck teeth he had before.    
  
That’s when it finally clicked. This was real. Tyler wasn’t hallucinating because of a bad trip. He was actually in a sewer somewhere beneath the town being targeted by a freaky clown creature that in no way could have been human after the things Tyler had seen.    
  
Tyler wanted to shout, or to cry. Everything in his gut was telling him to react appropriately to the world-shattering realization that he was experiencing, but instead, he was calm. His breathing stilled, as he scoffed at the clown, who had released his grip slightly around his neck, probably to encourage a verbal reaction.    
  
“I’m not afraid of you,” Tyler spat at Pennywise, meeting the clown’s hateful glare with one of his own. “I don’t feel anything anymore.”    
  
A slight twinge of something fell over Pennywise’s face, fracturing his menacing appearance. Though it was only for a split-second, it was there, and Tyler had caught it. He thought that it might have been confusion, or perhaps annoyance. Maybe even pity. Whatever it was, the clown had betrayed himself, and Tyler didn’t miss it.   
  
Pennywise drew him in then, pressing his plush red lips against the shell of Tyler’s ear as he crushed the human’s delicate body against his chest. “Let’s play a game.”    
  
The clown shoved Tyler back, releasing his grip on him and forcing him to trip, falling hard to the ground. Instinctively, he began to crawl backwards to distance himself from the menacing creature. He stopped only when he reached a wall and couldn’t go any further.   
  
Pennywise leapt forward, crouching down at Tyler’s feet, his hands resting on the ground with his long legs bent as he perched himself in front of his victim. He was the predator to Tyler’s prey. The clown breathed heavily, licking his lips in anticipation.    
  
Tyler realized that he was trapped. There’s no way that he could outrun this thing. He had nowhere to go and there was nothing he could do or say that would possibly spare him.   
  
“What’s the matter? You don’t want to play?” Pennywise teased through dark chuckles. “No jokes this time? That’s what you count on, isn’t it, Tyler? To be the funny boy?”   
  
“Stop,” Tyler warned through gritted teeth.    
  
“Poor funny boy!” Pennywise continued in a sing-song voice as if he hadn’t heard him. “So starved for affection! Oh, nobody wants to kiss the funny boy!”   
  
Tyler’s eyes narrowed, as if daring the clown to continue his taunts. “Back the fuck off and leave me alone.”    
  
Pennywise considered that as an invitation. “Alone? You’ve always been alone!”   
  
The clown threw his head back and cackled loudly, relishing in his own demented sense of humor. Tyler looked around, frantically trying to find anything that would help him out of the situation. There was no way he was dying like this. Not after what he had already survived. But there was nothing to aid him.

Pennywise growled out his name, his golden eyes shimmering in the dark, filled with malice, still taunting the young man. He bent forward intimidatingly. His face was so close to Tylers that their noses almost touched. “Kiss me, as if it were the last time...”    
  
Tyler saw an opportunity. In a desperate panic, he wrapped his hands around the back of the clown’s neck and yanked him forward, crashing his lips onto Pennywise’s chapped, red-painted ones.    
  
Pennywise paused, his eyes wide with confusion as he was taken aback by his victim’s unexpected actions. He was hardly ever taken by surprise.    
  
Tyler couldn’t believe that he had resorted to that. He didn’t even understand why that thought had even crossed his mind. He supposed it was a last-ditch effort to preserve his life. If nothing else, it was proving to be a somewhat decent stalling tactic. 

The kiss was soft, but firm as Tyler kept himself latched to the clown. Only after the initial uncertainty wore off did he start to move his mouth, encouraging Pennywise to do the same.    
  
The clown didn’t move, but he didn’t make any effort to push Tyler away, either, which he was grateful for since he was actually starting to enjoy himself. He released a soft exhalation of appreciation - almost a groan as he tasted the creature’s lips. The taste was bitter with an underlying sweetness that he found himself craving more of. It was as if he was tasting his childhood, but only the good parts. Though they were few and far between, they existed, and somehow this creature had the memories captured in his saliva, enticing Tyler in the best way.   
  
Finally, Tyler broke the kiss, releasing the clown’s costume and leaning back to gauge his reaction. His body was trembling with anticipation, betraying his attempt to appear confident. 

Pennywise placed the tips of his gloved fingers to his puffy lips, the bewilderment still present on his face before he broke out into a Cheshire Cat grin. “Tsk, tsk, tsk.” Tyler’s body went rigid. “You’re playing a game you can’t win. You see, I know your secret!”    
  
Tyler’s breath hitched, knowing that he only had seconds to come up with a response. He had to make it convincing. “I have nothing to hide. You want the truth? I’m into this. I’m into you. You want to take this further, I’m game.”   
  
Pennywise squinted at him in suspicion. “So you want to play?” Without waiting for a response, the creature bent forward, placing his nose in the crook of Tyler’s neck, sending shivers up his spine. “You don’t smell right. Not enough fear. There’s something else,” he murmured against Tyler’s skin.

“I-it’s probably arousal…” He knew it was a long shot. He was probably going to die there, but he couldn’t bring himself to care anymore. Hell, had it not been for the clown he would probably be belly-up in the river and already dead.    
  
Pennywise snapped his head back, wrinkling his nose in what appeared to be disapproval. “You wish to mate with a creature such as myself?”

Tyler nodded, swallowing thickly. “I mean, you did save my life and all. The least I could do is show you some gratitude, yeah?”   
  
It was hard to sell - he knew that, but there was also a small part of him that realized it wasn’t a lie. He already knew that he was fucked up in the head. It wasn’t much of a surprise that he would get off on being threatened by a strong creature that had obvious power over him. He found it alluring and twisted as it may be, he would be far from repulsed if the clown decided to accept his offer. 

Little did Tyler know, Pennywise knew his thoughts, his emotions, his desires, and his secrets that he kept locked away in his mind, so deep, that he had forgotten they were even there. Though the clown preferred children as a meal, there was something about Tyler that had intrigued him from the moment he had laid eyes on him after his long rest. He was a rarity.    
  
One of the reasons Pennywise never targeted adults was because they were difficult to intimidate. Not impossible, but children frightened far more easily, and the minds of adults were simpler to manipulate into thinking that nothing was wrong.    
  
Typically, Pennywise would have to resort to using his influence to impart despair into his victims so that they would understand that death was inevitable and that there was no use in fighting. Of course, that was only after Pennywise had his fun and tormented them for a bit for his own amusement. However, with Tyler it was different. He didn’t need to use that tactic because the human was already filled with enough despair and hopelessness that what should have been easy prey turned out to be something else. Something intriguing. Pennywise wasn’t quite ready to dispose of him yet.    
  
Tyler would succumb to his fate eventually. Pennywise was sure of that. They all did. Though he was curious to see Tyler come undone in the process. Unlike the others, Tyler would give into him fully and without reservation.    
  
The pleasure he took from the hunt was insurmountable. When his prey was finally in his grasp, he relished the feeling of their soft, warm flesh peeling away from their bones and their piercing screams ringing out in vain as they choked on their own blood. The sensation of watching the light leave their eyes as he lapped up their blood and devoured their hearts was as close to erotic as he had ever known. Until now. Fear sustained him over the course of his immortal life and the millennia that he had spent among humans, but now something else was taking root. 

Since Tyler had offered himself to Pennywise willingly, even after knowing what he was, the clown struggled to comprehend the emotions emitting from the human. Never had he experienced the urge to reflect or understand human emotion, because he cared little for what they felt. His way of life was limited to action and fueling the next hunt before his long rest, only to do it all again nearly three decades later. 

Pennywise never felt regret or hesitation towards anything. However, the thought of exploring Tyler’s offer was enticing. Part of him was angry for allowing a human to tempt him with something other than his life. It would seem that Tyler caused Pennywise to question himself and allow his instincts that preserved that part of himself to falter. He remembered the first moment he saw Tyler, alone and defenseless, strolling down the street with a cigarette in hand, lost in his own suffering. The aroma was intoxicating, but not in the way that Pennywise had sensed before. He should have just killed him, so why didn’t he? What power did this human have over him?    
  
Something that Pennywise would never admit to himself was that a part of him craved the feeling he got when he was around Tyler. It was a new discovery, and he was drawn to him. He needed him. Never before had he been so gentle and patient with a human. With Tyler, he knew that what he wanted from the human wasn’t fear, but something else worthwhile that he had yet to partake in. Not that Tyler would give into fear anyway. The human was broken, his soul darkened, and Pennywise wanted it all for himself, consequences be damned.   
  
Before Tyler could comprehend Pennywise’s actions, the clown had grabbed him harshly by the front of his shirt, yanking him forward so that they were pressed tightly against one another. Less than a second later, a strange pressure surrounded the two of them, making Tyler feel slightly nauseous until it passed as soon as it began. Glancing around his new surroundings, he discovered that they were in his bedroom - his  _ actual _ bedroom this time, and not just an illusion that the clown had created.    
  
Pennywise released Tyler’s shirt, allowing him to stumble back while his fiery eyes glowed in the dimly lit room, taking in every bit of the human before him before he opened his mouth to speak.

“Show me.”    
  
Tyler. didn’t need to be told twice. 

The man surged forward, grabbing Pennywise by his fluffy collar and yanking him harshly towards him to crash his lips against the clown’s painted red ones. As soon as their lips made contact, it was as though nothing else was relevant and everything bad that had happened over the course of his life had melted away. None of that was as important as this moment. It was a new sensation that Tyler had never come across. The only thing that mattered was that Pennywise was there with him and that he seemed to want Tyler just as much as he wanted him.

For a creature that Tyler imagined hadn’t spent much time romanticizing humans, he seemed to know exactly what he was doing. Despite the strange situation Tyler had found himself in, it was difficult not to appreciate the way the clown tilted his head so that their noses didn’t bump, or that his lips were full, but not overpowering. There was also the fact that his breath was shockingly fresh, despite what his diet seemed to consist of. On top of that, Tyler appreciated the way one of his long arms curled around his back to draw him in even closer while his other hand clung to his waist roughly, not in a painful way, but enough to let him know who was in charge of the situation. 

Almost forgetting that he required air to breathe, Tyler broke the kiss, inhaling deeply as he canted his head back, shivering while Pennywise continued his exploration with his mouth. The clown growled into his neck, using his buck teeth to nip and kiss his way down to his clavicle.    
  
“Mnf. Fuck… please?” Tyler whined, desperation evident in his voice. Pennywise smirked as he pulled back, basking in Tyler’s neediness. He then seemed thoughtful for a moment, as if he was contemplating something before he placed the tips of his fingers into Tyler’s mouth. Somehow Tyler had an inkling as to what he wanted, so he bit down slightly, holding onto the material of the glove as Pennywise pulled his hand back, revealing a surprisingly normal-looking human hand beneath, complete with long and slender fingers.    
  
“Hmm,” Pennywise hummed teasingly, placing his still gloved hand over Tyler’s obvious arousal. The jolt of need went straight to his head, sinking into his bones. “Please what?”    
  
“P-Please…” Tyler began, biting his lip with need. “Please… Daddy.” His dick twitched at his own words. He was pretty sure that there was already a damp spot on the front of his jeans. Calling him Daddy made him feel dirty and wrong in the best way. It had felt so natural and oh so perfect.    
  
“Good boy,” Pennywise murmured before he slammed Tyler to the ground, knocking the wind out of him as he fell hard to his hands and knees. In an instant, Pennywise had torn off his clothes, shredding them in the process and leaving Tyler bare apart from his black socks that still clung to his feet. Tyler shook, trying to comprehend how close Pennywise was to slashing his skin rather than just his clothes, but he surprisingly seemed unharmed.    
  
Daring to glance up, Pennywise’s once golden eyes were flashing as his grin stretched across his face. Knowing Tyler was watching, the clown slowly stuck out his tongue to an unnatural length, wrapping itself around two of his naked fingers, wetting them before he too got down on his knees and without any hesitation slipped two fingers into Tyler’s eager hole. Tyler gasped and keened at the rough treatment, relishing in the contact. Tyler was already bucking into his hand with an intense need. How did Pennywise even know what to do? The thought haunted him.    
  
Tyler was taking the initiative to grind back against his fingers, not caring how desperate he looked. He was suddenly yanked back by his hair and pulled up against Pennywise’s front. The clown pressed his lips to Tyler’s ear and murmured, “That’s it, little human. Fuck yourself on Daddy’s fingers.” Pennywise then forced Tyler’s head to turn so that he could kiss him roughly. Tyler moaned into his mouth, his hole clenching at his filthy words and harsh treatment. The clown then curled his fingers expertly and brushed against Tyler’s prostate, causing him to shudder. Pennywise began to fuck him harder and faster, adding a third finger and Tyler could barely take it. He whimpered and cried out shamelessly, feeling nothing but pleasure at that point. 

“Oh so tight and warm. Perfect. Delicious. Can’t wait to tear you open.” His words should have frightened Tyler, but they didn’t. Instead, it made him want Pennywise more. When he felt the clown’s hardened length through his silk suit against his back, he groaned and leaned into it. He felt big. Terrifyingly so. His heart pounded in his ears in time with his throbbing cock. Fuck, he was going to come. He didn’t want to yet. He never wanted the sensation to stop. It was unlike anything he had ever felt before, and he wasn’t ready to let it end. Pennywise’s fingers were magical, dancing along his insides expertly. It was better than anything he’d ever had.    
  
“Yessss,” the clown hissed, feeding off of Tyler’s erotic energy. He groaned when he felt Tyler tightening on his fingers. “That’s it. Come for Daddy.”    
  
That’s all it took. Tyler was sent right over the edge with just a few simple words. His back arched and he cried out as the most powerful orgasm washed over his entire body. Pennywise refused to let up as he fucked Tyler through it with his fingers, drawing it out, causing the human’s eyes to roll into the back of his head.    
  
He collapsed against Pennywise, his chest rising and falling dramatically with each breath. Pennywise slowly removed his fingers, earning a whine from the fragile human and flipped him around so that he was facing him. He held onto Tyler’s arms to keep him upright, sensing that his muscles were still recovering from his climax and would probably collapse beneath him. 

Tyler gazed into the clown’s fiery eyes, before pressing his lips softly against his mouth, breathing him in and feeling a warm sensation fill his chest. He was quickly growing attached to Pennywise. Perhaps he was the missing piece that he’d been craving all his life. However, even with that newfound adoration, he couldn’t suppress the uncertainty nagging at him.

“Pennywise,” he began as he reluctantly broke the passionate kiss and gingerly pushed him away, “Are… are you going to eat me when you’re done with me?”

Pennywise took a moment to inspect his face, seemingly trying to determine why Tyler was suddenly so focused on his own morality when he should still be dazed from lust. “Would you like that?”    
  
Tyler frowned. “C’mon. Seriously.” He knew that he was probably getting way too uninhibited with the creature, but he figured that since they had already crossed the threshold of having his fingers in his ass, he may as well ask. 

The clown bared his teeth in annoyance, but answered anyway. "Do not flatter yourself. I have little desire to feed on your flesh. You and I share a darkness. A void. An endless hunger that can only be satiated by each other,” he admitted while pushing a strand of hair from Tyler’s face as his yellow eyes rested on Tyler’s own emerald ones. “It is… natural to be drawn to one another.”

Pennywise’s words only made Tyler desire him more. He realized that ever since they had met, he had been infatuated with him for a reason. It wasn’t by chance. It was like they were always meant to find each other. 

“I mean…” Tyler began, choking on his own words, trying not to sound too emotional. “I’m obviously attracted to you, but I don’t know if I should be doing this. I want you… so badly, but part of it feels strange. You’re not human. You’re an entirely different species. Are you even able to...” he trailed off, eyes flickering to Pennywise’s smooth groin.

Pennywise then gripped Tyler’s hand in his own giant one and began stroking the topside of his hand with his thumb tenderly, a rare expression of affection. Either that, or it was a tactic to soothe his prey before he swallowed him whole. Whatever the reason, the simple gesture calmed Tyler as he squeezed his hand reassuringly in return. “We are compatible,” Pennywise assured him with a teasing grin.

Tyler met Pennywise’s piercing gaze with his own conflicted one. There was so much that he wanted to say to him but couldn’t find the right words. 

Tyler never got the chance to speak as Pennywise closed the gap between them and kissed him fiercely, hungrily moving his lips against Tyler’s with a desperate, unspoken need.

Without further warning, Pennywise impatiently lifted them both to their feet, sweeping them across the room before shoving Tyler onto the bed. Tyler let out a shocked gasp as his back hit the sheets and Pennywise transported himself on top of him in the blink of an eye, his weight pinning him down, which caused a stir in Tyler’s groin. He was already getting hard again.

Continuing the kiss, Tyler moaned against Pennywise’s mouth as his tongue demanded entry, to which Tyler happily accepted. Pennywise in return relished in the human’s taste as he explored his mouth before he eagerly took Tyler’s bottom lip in between his teeth and pulled gently, careful not to rip out his lip ring, despite the fact that he wanted to taste his blood. He released it shortly after and instead began to place soft kisses along his jawline while Tyler breathed heavily with arousal.

Tyler’s hands wandered all over Pennywise’s body, the smoothness of his silky costume feeling sensational. His hands made their way to Pennywise’s strong abdominal muscles that he could feel even through the material before descending lower to explore his private region. Tyler halted when his hands made contact with the prominent bulge in Pennywise’s groin.

Tyler kissed him tenderly and began rubbing him through his costume. “Mmm, like what you see, Daddy?” he breathed against his mouth. “Do I excite you?”

Pennywise growled with arousal, his entire body radiating desire and lust. Finally, a thick appendage emerged from his lower half, springing free of its confinement. 

Sneaking a peak, Tyler wasn’t sure what he had been expecting, but it certainly wasn’t what he saw. He was right about the size of it, but that was about it. The large organ was black at the base in comparison to his pale skin. The hue had faded into a deep maroon the closer it got to the tip, which was flared and leaking black ooze. The shaft was littered with plum-colored bumps and ridges that appeared to be writhing, as if his cock was literally pulsating with arousal. Just as he was coming to terms with the clown’s otherworldly organ, a thin wiggling appendage emerged from the tip of his cock only for a moment before the tendril dipped back down, hiding in the alien shaft. Pennywise smirked at Tyler’s obvious infatuation with his cock, and waited for him to get his bearings. 

Swallowing thickly, Tyler forced himself to snap out of his daze, completely hypnotized by Pennywise’s anatomy. As much as it probably should have repulsed him, he couldn’t wait to taste it. He then stumbled off of the bed and fell to his knees onto the floor before crooking his finger to silently request Pennywise to scoot closer to the edge of the bed for easier access. He angled himself over him and kissed each side of his silk-covered hips as the clown arched his back with anticipation. 

Tyler had then wondered if Pennywise had ever experienced anything like sex before. Would sex with his kind be similar to human sex? Whatever the answer, Tyler was going to do his best to please him, though that wouldn’t deter him from playing with him a bit. Just to be a dick, he pursed his lips and blew air over Pennywise’s leaking tip, causing him to sit up and glare at him, flashing his needle-point teeth in frustration. “Do not tease me, Tyler. It will be the last thing you ever do.”

Despite the very real threat in his warning, Tyler chuckled as he pushed on his chest, forcing him to lay back on the bed. Pressing his luck, the man mumbled, “Don’t complain or you won’t get anything at all.” Pennywise should have ripped his throat out, and for a moment, he contemplated doing so. Instead, he calmed himself, knowing that it was just a matter of time before he got what he wanted. He always did, and this was no different. He snarled in response but remained silent as Tyler positioned his mouth over his fully erect inhuman cock.

He ran the tip of his tongue lightly over Pennywise’s slit in small kitty licks, causing him to inhale deeply, but he didn’t complain or move. Tyler noted that the black ooze tasted sickly sweet, but also savory. With a little more force, he ran his tongue along one of the violet veins underneath his cock. Tyler felt his body tremble as he took each of his balls into his mouth, one by one, sucking gently while pumping him slowly, barely causing any friction. Pennywise almost whined at the sensation, but would never give the human the satisfaction of knowing how incredible it felt. It wasn’t like him to put himself in such a vulnerable position, but he was too far gone as Tyler continued nuzzling against his scrotum, reveling in the effect it was having on the clown.

Tyler had figured that he had teased him enough at that point, and was getting impatient himself, realizing how much he wanted to please him. Abruptly, he engulfed the head of his dick, sucking harshly as Pennywise pushed his hips forward, desperate for more contact. “More...” he demanded as Tyler took more of his cock into his mouth.

Tyler hummed in approval as he circled the head of his bulbous length with his tongue before digging into the slit. Pennywise couldn’t help himself and released a low groan in approval. Tyler hollowed his cheeks and started to deep throat him, swallowing his length as his head hit the back of his throat. He gagged a bit and felt the tears welling up in his eyes, but he kept going, knowing how good it was making him feel.    
  
Strangely, he was not as affected by the inhuman organ in his mouth as he thought he would be. He was apprehensive at first, but he seemed to actually enjoy the taste and the texture of the oversized cock in his mouth. 

“Yes, just like that,” Pennywise urged as Tyler sucked him harder, grazing the underside of his cock with his teeth. “Take it-t,” he emphasized the last syllable with a click of his tongue. 

Tyler knew the clown was close when he grabbed Tyler’s hair roughly, the tips of his claws grazing his scalp. His back was arched severely and he was trembling with loss of control. Tyler was shocked to see him this way. Pennywise seemed to be a creature that was always so in control and now he was melting into his bed, completely at his mercy. 

Suddenly, Tyler felt a blissful sensation radiating throughout his body. He had been so focused on pleasuring Pennywise that he hadn’t noticed the multiple appendages snaking their way out of Pennywise and onto his own naked body. 

He choked on Pennywise’s dick, not expecting to see actual fucking tentacles sprouting from the guy that he was sucking off. One of them had slipped down between his thighs and began to attack his groin, which caused him to pull back, earning a feral snarl from the other due to loss of contact. Pennywise released the hold on Tyler’s hair and began to retract his tentacles back into his body. Still trying to come to terms with his situation, Tyler gawked at the slimy limbs before they disappeared into his silk suit. “Pennywise, fuck- I don’t… This is a lot to take in. I know you’re not human, but you can’t just-”

“Do not tell me what to do!” Tyler flinched as the clown snapped at him, his teeth elongating once again into jagged daggers as he glared threateningly at his inferior. “You will bend to my will or you will rot among the weeds!” He demanded, running his tongue enticingly along his fangs.

Acting on instinct, Tyler swallowed thickly as he took Pennywise’s cock in his hands again. He stroked him faster, squeezing slightly and flicking his thumb over his heavily leaking slit. Pennywise’s eyes practically rolled to the back of his head as he relished in Tyler’s skilled movements. It was almost better than fear. Almost.    
  
“Let go, Tyler. Be afraid. You’ll taste so much better when you’re afraid.” The clown cackled, at his own wording, as if he was laughing at his own inside joke. “Oh, you are priceless, little human. I am eternal. I am the eater of worlds and if you continue to oppose me, you will regret it.”

Tyler groaned outwardly at his harsh words that ignited something inside of himself and he couldn’t find a reason to protest. He reached down and grabbed his own erect dick, giving it a couple of pumps as he enveloped Pennywise’s thick cock once more, making obscene slurping noises as he bobbed his head up and down over his length.

After a few moments, Pennywise’s additional limbs had returned to Tyler’s body, pushing his hand away and continuing to jerk him off as the unbelievable pleasure continued to surge through him. Not only did the tentacles seem to have skilled movement, but there was an aura radiating from them that caused a blissful sensation, making it feel like every inch of his skin was covered in an erotic tingling. Tyler started to lose his rhythm as the feeling became rapidly overwhelming, but he was still focused enough to flick his tongue in all the right spots, causing Pennywise to groan loudly, only increasing his drive to bring him over the edge.

Not long after that, Tyler felt Pennywise’s dick twitch violently inside of his mouth. Pennywise’s chilled cum had lined the back of his throat with each heavy spurt. A downright terrifying shriek emitted from Pennywise’s throat as he released inside of Tyler’s mouth, his claws digging into the sheets beneath him, tearing them to shreds.

It was as if his release heightened the nerves in his tentacles, because as he was spilling himself into Tyler’s mouth, the pleasurable sensation escalated immensely, instantly bringing Tyler to his own release. He pulled himself off of his length and shamelessly moaned in bliss as his own orgasm ripped through him violently.

When he was done emptying his load onto the carpet, he took Pennywise’s cock into his mouth once more to lick up any remnants that may have been left behind when he pulled off. Pennywise purred lightly as he sucked him, appearing weak from his release and oversensitized. However, Tyler was shocked to find that instead of his dick softening, it was becoming more erect. 

When he looked up at Pennywise, dumbfounded, his gaze was met with a wicked grin as Pennywise understood his confusion. “What’s the matter, Tyler?” he teased. “Can’t keep up?”

Pennywise surged forward, kissing Tyler sloppily and passionately before leaning back and gazing down at Tyler’s nude figure. Tyler’s face flushed as he noticed Pennywise’s gaze raking over him. He licked his crimson lips and a small moan escaped him as he lifted his hand to slowly drag the pads of his fingers across Tyler’s chest. When his eyes met Tyler’s again, his smile widened. “You’re mine, Tyler. Time to float!”

Tyler couldn’t stop himself from kissing Pennywise again, grinning at his possessive words while Pennywise shoved his tongue into his mouth. He pressed himself up against Tyler, making his arousal that much more obvious. The feeling of his body against Tyler’s was extraordinary and a very different experience than any other interaction he’d had with a human.

Without warning, Pennywise suddenly lifted Tyler into the air and carried him over to the other side of the room where his desk was. Using one of his tentacles, he shoved everything off of the top of the desk to set Tyler on top of it. The wood was cold against his bare flesh, but that was soon forgotten as Pennywise began licking long languid strips over his neck, his tongue flicking gently as he made his way down to his chest, making Tyler shake with anticipation. Much to his own surprise, his refractory period was quickly fading, and his length was hardening once again.

He whimpered as Pennywise took both of his nipples into his fingers and squeezed gently. He then settled his mouth on one of them, moving his tongue all around the hard flesh. Tyler bit his lip trying to contain the moans that were building up inside of him again. However, the cries of pleasure soon shot out of his mouth when he felt Pennywise’s tendrils crawling up his skin, igniting his senses and pleasure points. 

“Please,” he begged through his arousal.

Pennywise smirked, looking at his new toy with a sense of victory, enjoying the fact that he was back in control. “Tell me what you want, Tyler.”

“You,” he crooned, trembling beneath his touch. “I just want you.”

Pennywise grinned mischievously, accepting the challenge that Tyler had unknowingly set for him as his mouth returned to his chest and his hand grabbed Tyler’s strained cock. He groaned wantonly as Pennywise pumped him faster, teasingly licking his way down to his crotch.

Tyler half expected him to tease him as he had done to him earlier, but to his surprise, he wasted no time in taking him into his mouth, sucking on his head harshly, swallowing the pre-cum that had already formed. “Fuck, Penn,” he muttered under his breath as Pennywise deep-throated him with inexplicable expertise, purring at Tyler’s new nickname for him.

Too soon, he pulled off and stood back, smirking at Tyler’s flustered impatience. “What are you doing?” he asked, failing to disguise how desperate he was for Pennywise at that moment.

“Turn around,” he commanded bluntly.

“What?” he huffed, confused, getting more impatient by the second. “Already? But, you-”

“Turn. Around.” He twirled his finger for emphasis to motion for Tyler to obey.

Eyeing him suspiciously, Tyler did as he asked, sliding off of the desk and facing the wall.

“Lean against the desk.”

“Pennywise-”

“Tsk, tsk, tsk,” he interrupted. “This is your last warning. Disobey me again, and you won’t live long enough to scream before I rip your lungs out through your chest and devour them whole.”

Tyler sighed in frustration, but he did as he was told, bending over the desk and resting his hands on the wooden surface. He flinched as he felt Pennywise’s large hands between his thighs, pulling them apart, causing him to instinctively spread his legs.

Whatever he had been expecting, it definitely wasn’t what Pennywise was planning. Before he could properly prepare himself, he felt the clown’s long and rough tongue lap at his entrance. Tyler’s arms instantly gave way as he melted into the desk at the sensation. “Fuck! Oh my god, P-Pennywise,” he mewled as the creature’s tongue continued to delve into him with blunt force.

Incoherent syllables escaped him as Pennywise continued exploring his entrance. It was almost too much to take. He could feel the blood circulation leaving his hands as he grabbed onto the side of the desk for dear life, his legs trembling at the pleasure radiating through him. Tyler writhed against him as Pennywise’s chilled and wet muscle pumped in and out of him. He almost lost complete control when Pennywise’s tongue stretched far enough inside of Tyler that it found his prostate with ease, rubbing against it firmly. Tyler choked on his breath as his legs continued to shake, his knees buckling as the rough texture of Pennywise’s monster tongue caressed that sweet spot that made him see stars. 

Before he went completely over the edge, Tyler straightened up and quickly turned around, forcing Pennywise to retract his tongue before Tyler pushed him back aggressively. Pennywise barely moved since Tyler’s strength was insignificant in comparison to his own, but he still gave Tyler a perplexed expression as he waited for an explanation, clearly wondering what he had done wrong.

Tyler was sure that his expression was animalistic as he reached forward, digging his nails into the arms of Pennywise’s silk suit before pulling him around so that he could push him into the desk chair. Pennywise fell into it with a growl, and then chuckled darkly.

Tyler then straddled him and imitated the clown’s moves from before by kissing his way down his neck, occasionally nipping softly, making Pennywise hiss in excitement. However, as much as Pennywise was enjoying the affectionate bites, he wasn’t yet ready to give up control again. 

In the blink of an eye, he had reversed the roles yet again, forcing Tyler into the chair that he had been in moments ago. The menacing creature then got down on his knees, eyeing Tyler hungrily. Tyler swallowed thickly, struggling to comprehend that an all-powerful being such as Pennywise was getting on his knees for him. 

Clearing his throat awkwardly, Tyler mumbled, “Uh… you know, you don’t have to do this. I’m used to being the one who pleases others. I don’t even really need anything in return,” he babbled nervously, going red in the face and glancing between Pennywise and his own cock, which was practically weeping for attention. 

A smug grin graced his red painted lips as he gripped Tyler’s length in one of his large hands, stroking it teasingly slowly at first, but soon sped up, making Tyler’s breath hitch in his throat. “You’ve dreamt about having an experience like this for some time, Tyler.” Pennywise gave him a challenging stare, which he hardly noticed because he was too focused on the clown’s skillful hand twisting around his dick, the thumb running over his slit with each upward stroke. His voice was laced with lust and longing, which had more of an effect on Tyler than he cared to admit. “I want you to have everything you desire. If you’re loyal to me, I’ll give you everything you’ve ever wanted.”

“S-so this… mnph… this isn’t j-just a - oh god - a convenient fuck… f-for you?” Tyler barely managed to let the words pass over his lips as he tried to keep his breathing even. He knew that Pennywise could tell how he was practically putty in his hands, but he didn’t want to give him the satisfaction of completely giving in. “Y-you don’t need to… coddle me.” 

“Shhh. There’s no need to spoil our fun. Just relax and enjoy what I’m about to do to you. After all, it’s not often I partake in this kind of game with humans. Let me take care of you. I can be your mate, Tyler. I can be whatever you want me to be,” he murmured softly. “I can be  _ whoever _ you want me to be.” 

That got Tyler’s attention. He hardly had time to register what it was that he was proposing before his lips wrapped themselves around his throbbing length. “Oh, fuck,” he whimpered under his breath, earning a stimulating hum from the clown. He seemed shockingly good at this considering he didn’t seem to engage in this activity often… if  _ ever _ . 

“Please,” he helplessly continued to beg. “I need this… I need you, Daddy.” As soon as the words left his lips, the clown sunk lower onto his cock and he could feel his tip hit the back of his throat. Tyler choked out a loud moan, closing his eyes and throwing his head back as Pennywise kept him in position, gulping down the precum on his slit, not gagging even once. He seemed to be completely unfazed and had no gag reflex whatsoever. 

Tyler’s thoughts were interrupted when two tentacles sprang from Pennywise and wrapped themselves around his thighs, lifting him off of the chair slightly. Something then began to prod at his lips. Opening his eyes, he barely registered the dark tentacle before it jutted past his lips and into his mouth, swirling all around, gathering his saliva. It tasted sweet, leaving behind a sticky and tangy secretion before it slipped out and traveled below to his eager hole. He had a feeling of what was coming, but he still wasn’t fully prepared as the tentacle abruptly inserted itself into him. A low groan involuntarily erupted from his throat as the burn turned into a friction that he desperately needed more of.  
  
“That’s it, Tyler,” he heard Pennywise whisper over his own desperate panting. “What a thrill to see you this way. This is how you should always be for me. Needy. Compliant. Willing to do whatever I say as I feast on your flesh and feed on your fear!”

“Mmm, yes, Daddy! Take me! Do whatever you want to me. I just- oh, fuck yes!” Tyler practically sobbed when Pennywise’s mouth returned to his dick while his skillful tongue wrapped itself around his length, milking him. The clown then added a second tentacle to his hole, sliding in deeper to find his prostate, rubbing against it mercilessly. Tyler didn’t think that it could get any better until he felt a mind-blowing and powerful surge radiating through his body, sending him to the brink of insanity from the amount of pleasure stimulating his form all at once. 

Pennywise really was magical. Tyler could suddenly feel everything as though it was magnified. Every touch. Every lick. Every breath. It was every arousing touch he had ever experienced, but tenfold, and his body couldn’t hold out any longer.    
  
Tyler wanted to cry when Pennywise removed his mouth from his throbbing cock and lifted his head up to meet him at eye-level. “I want you to remember how this feels,” he stated in a husky voice. “I want you to see that only I can bring you this kind of pleasure and that no one else will ever have you because you belong to me.” His hand sped up to stroke him roughly while his tentacles worked their magic inside of him, thrusting against his prostate in just the right spot. Tyler could feel the familiar coil in his gut starting to tense up, ready to unravel at any moment. 

Tyler didn’t want this to end. He tried to fight it off. He closed his eyes and tried to picture anything that would distract him from his inevitable release, but Pennywise wasn’t having that. “Look at me, Tyler,” he snarled. 

“I-it’s too much!” he cried back at him. The words hardly left his lips before the creature’s mouth was covering his own, diving his tongue in to taste him. Tyler’s eyes snapped open in surprise. Pennywise quickly pulled back, meeting Tyler’s green eyes with his own dark, clouded and hungry ones. For a brief moment, Tyler didn’t feel overwhelmed by lust. He felt… warmth - an intimacy that he had craved all his life but never had encountered for himself and that was all it took.    
  
He thrashed and moaned loudly as the tension came undone inside of him and he spilled heavily into Pennywise’s hand. The clown licked his lips and smiled smugly as Tyler continued to cry out shamelessly into the air as the euphoria rushed through him. Pennywise removed his tentacles and his movement slowed a bit as the weak human continued to cum into his hand, but he never faltered until the last of the aftershock made its way through his system and he felt like he was melting into the chair. 

Through half-lidded eyes he could see Pennywise’s satisfied grin as he sensually licked his cum off of his hand, groaning at the taste of it. “Good boy,” he praised before he bent down to engulf Tyler’s softening cock once more to swallow down his remaining seed. Tyler choked on his breath at the stimulation and the way Pennywise’s tongue lapped at his sensitive flesh, but it was still enjoyable. 

Pennywise stood up, staring down proudly at his prey and the pile of loose limbs that he had reduced him to. Tyler hardly had the strength to open his eyes, but when he did, he was greeted with the clown's prominent erection, begging for attention again. 

Tyler didn’t know if he could go another round. His body was already exhausted, but he couldn’t shake the desire that was consuming his mind. He wanted to have that cock inside of him, and he wanted it now.    
  
The tired human slid down onto his knees and looked up into the creature’s cold eyes with his own pleading ones, silently begging to take his throbbing member into his mouth again to prep him. “Are you ready to float?” Pennywise teased, flashing his buck teeth in a malevolent grin. 

“Yes, please,” Tyler crooned. “I need you inside of me.” Without further hesitance, he took Pennywise’s cock in his hand and began by running his tongue up and down his shaft. Tyler could feel him shiver against him. He then settled his mouth just around the tip of his girth and sucked gently, letting his tongue flick and swirl all around it. He looked up to see Pennywise close his eyes and open his mouth slightly, lips quivering and gasping slightly every time his tongue slid across his slit.

Tyler took as much of him into his mouth as he could at that point. Granted, there was no way that his entire length would fit, but it must have felt good because Pennywise threw his head back and groaned loudly with satisfaction. He began thrusting forward, fucking Tyler’s throat with abandon. Tyler would have trouble speaking later with the way Pennywise was wrecking his throat. 

With each thrust, the human bobbed his head, occasionally grazing the underside of his cock with his teeth just as before, which the clown seemed to really enjoy. Pennywise’s fingers tangled themselves into his blonde hair, forcing him further onto his shaft than he thought possible. Tears were forming as he struggled to repress his gag reflex, but he somehow managed. However, the point wasn’t to get Pennywise off just yet. Tyler knew that this was only preparation for what was coming next.

He should have known that Pennywise would catch on, considering he seemed to have a front row seat to his personal thoughts. When Pennywise released his tight grip on his hair, Tyler smiled playfully at him as he removed his mouth from his length, which earned him a forceful lift back onto the edge of the desk. 

Pennywise kissed him hard and brutally before pulling away and lining up his cock with Tyler’s hole. Tyler was nervous - he knew this would probably hurt. He had never taken a cock so big, but he had never wanted anything more in his life. He nodded and pulled the clown into another kiss as he slowly entered him. Tyler whimpered into the kiss as the thick cock pushed in further, inch by inch until the creature was fully sheathed inside of him. Tyler’s legs wrapped around Pennywise’s waist as he kept him inside of him for a minute, letting his head loll back as he adjusted to him. His legs relaxed when the pain started to fade, and Pennywise took it as a sign to pull back and enter again, but with a little more force. 

Pennywise’s movements were a bit sloppy and uncoordinated, just as it would be for anyone who hadn’t ever had such an encounter. Regardless of his clumsy and awkward motions, it was still extremely enjoyable. Tyler cried out in bliss with every thrust as his hips snapped forward. Pennywise’s head rested in the crook of his neck, showering it with nibbles and flicks of his tongue as he plunged harder and faster. Tyler’s arms wrapped themselves around Pennywise’s neck as he increased his speed, desperate for additional friction.

“Yes! Oh, Daddy, please!” He didn’t care how desperate he sounded. He was lost in his own bliss. All the pain was gone. The way Pennywise’s pulsating nubs and ridges grazed the inside of Tyler’s sensitive flesh was euphoric. “Fucking use me! Make it hurt! Fuck me as hard as you can!”

Tyler was once again taken by surprise when the creature growled and lifted him up, his member still deep inside of him as he made his way to the bed in an instant, toppling down on top of it and then continuing to thrust violently inside of him. Tyler’s legs once against wrapped themselves around him, pushing him in further. Pennywise had shifted his angle slightly and Tyler cried out shamelessly when he found his prostate.

“Penn! Fuck… right there, Daddy, please! Don’t fucking stop. Fucking  _ wreck  _ me,” he begged as his back arched in pleasure as the alien cock prodded at his sweet spot with each forceful lunge. He wasn’t even sure where those words were coming from, but Pennywise seemed to enjoy it. Immensely. What made it even more rapturous was the fact that he could now feel the small tendril that he had seen emerge from the head of Pennywise’s length earlier, now wrapping itself around his prostate, stimulating it in a way he had never felt. The pleasure was quickly becoming overwhelming and he knew he wouldn’t last much longer like that.    
  
Pennywise straightened up, lifting Tyler harshly by the hips to tip him forward, grunting animalistically in the process. Tyler let him position him with no resistance, allowing Pennywise to throw him around like a rag-doll. It was hot.    
  
As Pennywise inserted himself again, Tyler was mewling and whining, gripping the sheets in his clenched fists as he closed his eyes. He was splayed out attractively as Pennywise was pounding into him at a fast and unrelenting pace. His hands then moved to his ass to hold Tyler open, watching with fascination as his own cock slammed into Tyler’s eager hole. 

“Yes, yes, what a fun game this has been!” Pennywise grunted as he accentuated his words with each jab. Tyler could feel droplets of what he could only assume was drool spilling onto his back as Pennywise spoke. “This is a game I could play again and again! Much better than, say, Truth or Dare, right? Oh, you wouldn’t want anyone to pick Truth though, would you, Tyler? You wouldn’t want anyone to know what you’re hiding!” He cackled loudly, sending a shiver town Tyler’s spine as he groaned wantonly. The clown then began to sing at the same rhythm that he fucked Tyler to. “I know your secret! Your dirty little secret! Oh, I know your secret, your dirty little secret!”    
  
He stopped singing then to release a feral roar, which Tyler had hoped was a noise of pleasure rather than warning. He then pulled out for a moment and effortlessly flipped Tyler over so that he was on his back and was able to look right into Pennywise’s eyes as he claimed him. “Don’t worry, Tyler. Your secret is safe with me. I’m your dirty little secret now!” 

Pennywise’s words affected him more than he had anticipated. He was just on the precipice of oblivion as Pennywise fucked into him brutally. “Harder, Penn! Please, t-touch me! Fuck, please!” 

While Pennywise’s hands remained in an iron grip on his hips, three more tentacles emerged from his body. Two flicked and teased his nipples while the other gripped Tyler’s leaking dick, pumping furiously, knowing that it wouldn’t take long for his release. “Time to float, Tyler!” He warned, panting and holding Tyler tighter, trying to ensure that he reached his high before he did.

Moments later, Tyler tensed up as his orgasm approached. No longer able to hold back, his orgasm erupted from deep within his core, firing through every cell in his body while he practically screamed in ecstasy. It was so severe, he seemed to have blacked out for a moment. His heartbeat was pounding in his ears as he emptied himself onto Pennywise’s tentacles and his own stomach, his dick twitching violently with each spurt that never seemed to end. He had never cum so forcefully in his entire life. It was absolutely euphoric.

The pulsing feeling around his cock was more than Pennywise could take. Ignoring Tyler’s oversensitivity, he continued to thrust powerfully and erratically, chasing after his own release. He groaned loudly as it built up, causing his mouth to split open and reveal rows of needle-point fangs that seemed to trail all the way down his throat while a warm glow radiated from deep within his very essence. Something inside of him snapped, and he gripped Tyler’s hips so tightly that the tips of his claws broke through the skin as he released himself inside of the human, filling him with his alien seed. 

“Yesss,” the clown hissed hoarsely. “So good. So deep. How I’ve waited for this very moment…”

Tyler should have felt pain, but instead he was solely focused on the sensation of Pennywise cumming inside of him, his cock pulsating even more aggressively, splattering his insides with everything he had. 

When the aftershocks ebbed away, Pennywise fell forward weakly and rested on top of Tyler only for a moment before rolling over onto his back, his fangs and tentacles now retracted, returning his form back to its far less terrifying self. 

“Wow. Holy shit, Pennywise.” Tyler panted, thoroughly exhausted, but more satisfied than he had ever felt in his life. “That was just… I cannot believe that just happened.”

Pennywise’s only response was a dark chuckle. Even the clown seemed to be at a loss for words, still recovering from his own release as he lay beside the human with his eyes closed, his lust satiated for the time being.

Tyler shifted awkwardly, propping himself up on his elbow as he stammered, “Um. So, uh… are we… w-what happens now?”

The clown’s eyes opened slowly, his once golden eyes now sky blue as they gleamed brightly. His gaze fell upon Tyler’s hopeful face, but again, he said nothing. 

In an attempt to fill the silence, Tyler prodded, “I mean, were you lying before? Are you going to eat me? Or… is this going to happen again?”    
  
“Only if you’re a bad boy,” the clown finally replied, flashing a toothy grin. 

Tyler gawked at him, swallowing hard with nervousness. “Wait… the eating me part, or the sex part?”

Pennywise hummed thoughtfully, teasing Tyler with a wry smirk. “Fear not, Tyler. The fun is just beginning.” 


End file.
